If you haven’t booked your summer vacation yet, don’t fret. While most people go away in June, July and August, a trip to the Greek Islands is actually a great destination in September and October. Visitors will still enjoy the beautiful, balmy weather and warm, azure waters while also getting away from the crowds and experiencing the destination in a more budget-friendly manner.

I got the chance to visit these beautiful islands last September. After hearing about how crowded the popular ones like Santorini, Ios and Mykonos were, I was surprised to experience the exact opposite. Not that it was completely empty, but you can visit popular sites without feeling like a sardine in a can. Additionally, while my friends who had gone in July had spent about $1,800 for a round trip flight from New York to Athens, I spent only $875 going in mid-September. Not only are flights cheaper, but accommodation and ferry tickets often are, as well. Many cruises also offer special discounts in September as they reposition their cruise season. Additionally, there are many worthwhile events to attend, and you can go without having to fight other travelers for ferry reservations.

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Aside for the Halkidiki peninsula and the islands of Samothrαki and Thαssos, most of the Greek Islands are perfect to visit during shoulder season and will still cater to tourists. While each island has something special to offer, 10 that I highly recommend are Ios, Mykonos, Santorini, Paros, Naxos, Crete, Delos, Corfu, Rhodes and Skiathos.Santorini

Santorini is a pristine island, often visited by those who want a romantic getaway. Visiting the beautiful beaches, like Kamari Beach and Red Beach, is worthwhile, as well as seeing historical sites like Ancient Thira, an archaeological site from the Hellenistic, Roman and Byzantine eras and Ancient Akrotiri, a former Minoan outpost from the 16th century that was destroyed by a volcanic eruption. Additionally, you can attend the International Music Festival of Santorini in the first few weeks of September. This year’s event will be from September 2 to 16. Furthermore, 2012 will also offer the Santorini Bienniale, an art and culture event, which runs from now until the end of September.

Crete

Crete is an island with a lot to see and do. Some of the great beaches include Elafonissi, Falasarna and Preveli. If you don’t mind putting in a bit of effort, Balos Lagoon in the Kissamos area is difficult to get to, but well worth it for the crystal warm water, white sand and rugged beauty. If you like animals, Aquaworld Aquarium is a popular site, which can be visited until October 31. They have a large variety of marine species, and only take in animals that are in need of care. For a scenic experience visit Samaria Gorge National Park, often said to be one of the most beautiful national parks in Europe. In early September, you can attend the Labyrinth Musical Workshop with classes and events to learn about local and world music. Furthermore, in mid-October you can celebrate their annual Chestnut Festival, a fun day honoring the arrival of fall and chestnut-inspired foods.

Ios

While known as a wild party island, Ios calms down considerably by September. That’s not to say there isn’t nightlife – you’ll still be able to party and have fun – but it won’t be as crazy as when the backpackers arrive in the summer. For many, this is a blessing, as it offers a chance to explore the beauty of the island in a more peaceful manner. When I went, I stayed at Far Out, which has a hotel, bungalow and camping option literally right across from Mylopotas Beach. Ios is often touted as having the “Top 10 Beaches in Europe” when surveys are done, so exploring this and Maganari Beach is a must. Until mid-October, you’ll be able to enjoy water sports like windsurfing, waterskiing, wakeboarding, kneeboarding, kayaking, surfing, banana boats and tube rides. Other worthwhile activities include boutique shopping and admiring the whitewashed buildings in Chora, visiting the Venetian castle of Paleocastro and seeing Homer’s Tomb, the resting place of one of the greatest Greek poets in history.

Mykonos

This cosmopolitan destination is one of the most popular of all the Greek Islands, and for good reason. Because it tends to get overcrowded in the summer, visiting during shoulder season is a good idea. Visit the destination’s iconic windmills, stroll through the charming streets and get a cocktail in Little Venice, take in panoramic views from Armenistis Lighthouse, visit the Byzantine Church of Paraportiani and get educated at the Folklore Museum. And of course, a visit to one of the many beaches, like Panormos, a quiet beach with a mountain backdrop, Platis Gialos, a beach featuring calm water and a plethora of eateries and Elia, a clothing optional beach, is a great way to waste away the days in a beautiful setting. For a fun event, the Mykonos International Gay Film Festival will take place from September 10 to 16, 2012.

Paros

Paros is the second-largest island in the Cyclades, and features unique beaches, each of which has a different vibe. For example, Santa Maria has a Caribbean Island feel, while Kolymbithres Beach is unspoiled with unique rock formations, colorful water and no music or fancy lounge chairs to take away from the untouched feel. Other fun activities include visiting the first century Panayia Ekatondapiliani Cathedral, the old-world village of Lefkes and the Marathi Marble Quarries, which features a high-quality marble only found in Paros.

Naxos

Naxos is the largest island of the Cyclades, with opportunities for relaxation, adventure, culture and history. If you want to experience true paradise, head to Plaka Beach. This isolated beach features fine white sand, turquoise waters, barely any wind and even a clothing-optional section. For those seeking adventure, head to Agios Prokopios Beach where you can partake in water sports or sign up for a snorkeling or diving trip to see marine life and shipwrecks. For a bit of history, check out the iconic Portara, a marble gate from sixth century B.C., on the islet of Palatia in Naxos Harbor. It is the sole remainder of a temple dedicated to Apollo. And, for great photo opportunities, the Castro, or old walled city, is elevated above the harbor, awarding excellent views. Check out evening concerts at the Venetian Museum from September 1-30.

Delos

According to mythology, Delos was the birthplace of Apollo and Artemis, and there are many opportunities to explore this part of history. Visit the three temples of Apollo, the sacred lake where Apollo was born and The Alter of Dionysos. You’ll also get the chance to visit Cleopatra’s House, named after the two headless Cleopatra statues found inside. A theatre from the second to third century B.C., the Archeological Museum of Delos and the Avenue of Lions, a street from seventh century B.C., lined with ancient lion statues, are also worthwhile sites to check out.

Corfu

Located in the Ionian islands, Corfu has a history of being controlled by foreign powers like the British and the Venetians. Its rich history combined with its natural beauty make this a destination for all types of travelers. Moreover, the rainy season doesn’t come until November, so those looking to go in September and October will still be able to enjoy the sunny weather. During a visit to Corfu, make sure to explore the various villages on the island. There is Nymphes, full of waterfalls and legends of bathing nymphs and Roda, a mix of traditional fishing village and modern tourism. Moreover, Lakones features 18th and 19th century homes and churches while Kynopiastes has old mansions from the 17th and 19th centuries, a 17th-century monastery, a marble church and a museum dedicated to the olive tree. For something historical and peaceful, the British Cemetery offers a tranquil garden, hundreds of British graves and over 200 years of history. And, of course, the many beaches can keep you occupied for hours. Wine lovers will be able to take part in the annual Arillas Wine Festival, happening from September 7-8.

Rhodes

One of the largest Greek Islands, visitors to Rhodes will experience beaches, a medieval town, archeological sites and a rich history that goes back to Neolithic times. This island often has more than 300 days of sunshine per year, making it a great destination even during shoulder season. Travelers love visiting Rhodes for the mix of sandy and rock beaches, all with different atmospheres. While Lindos is a sandy and trendy beach, Gennadi is a popular surf spot. Additionally, Faliraki is a mix of sand and rock and is the island’s only legal nude beach, although tanning in the nude is tolerated in some areas of Tsambika. For some adventure with stunning views, climb to the top of Mount Attavyros. The climb takes about two to three hours and will take you up 3,986 feet in elevation. Moreover, some historical sites of the island include the Acropolis of Lindos, the medieval fortress and city sites of Ancient Rhodes, the Church of Panagia and the Palace of Grand Master of Knights. Some events to check out include Timiou Stavrou, a Greek dancing festival taking place from September 13 to 14, and the religious festival of Aghios Loukas on October 17.

Skiathos

Part of the Sporades Islands, Skiathos is a mix of cosmopolitan luxury and medieval history. While the main strip is more loud and boisterous, the other areas feature great hikes and quiet retreats. For some medieval history, visit Kastro, which was the largest medieval town from the 12th century until 1830. It was built upon a cliff sticking out into the ocean at the north end of the island, and although today the site is mostly ruins, it still offers expansive views of Skiathos and its surroundings. For a bit of relaxation, head to the beach. A beautiful sandy beach that allows nudity is Banana, which is actually composed of three beaches – Little Banana, Nameless Banana and Big Banana. Moreover, Koukounaries is the most popular and thought to be the “best in the Aegean,” Kanapitsa is good for water sports and Asselinos is quiet and romantic. My personal favorite beach on the island, however, is Lalaria. It is only accessible by boat, and features gray marble pebbles, unworldly rock formations and crystal clear water you can see through even in the deep areas. From September 19 to 22, visitors can attend International Festival Burtzi Skiathos, a Mediterranean folklore festival.

A new travel-planning website and booking engine is launching this month in beta, and I was excited to give it a test run, having first heard about the site this spring at a EuroCheapo travel happy hour. Wanderfly.com is a “personalized recommendation engine” that takes your interests, budget, and even social network connections to give you inspiration and help you plan your next vacation. Flights and hotels are pulled from Expedia, with restaurant recommendations, activities, and sightseeing descriptions culled from Lonely Planet, FourSquare, NileGuide, and Yelp.

Let’s say you have a week to travel in early September for Labor Day. Budget is under $1,000 per person for flights and hotels, and you’re interested in culture, beaches, and food. Plug all those into the search engine and you’ll get a series of destinations to review, refine, share, and book. While the site still has a few bugs (budget busters would sneak through the filters, the help feature is not fully enabled), the interface is slick and user-friendly, the features are thoughtful, and the content is reliable.

What’s cool about the site:

Since I’m currently based in Turkey, I loved that your point of origin could be pretty much anywhere in the world so I could run searches from New York and Istanbul to get a wide variety of places convenient for different parts of the world.

A wide (1,200 and growing) network of destinations gave me some ideas I’d never considered or even heard of (Kalingrad, Russia; Azemmour, Morocco; Krabi, Thailand), as well as some more tried-and-true vacation spots(Sunny Isles Beach, Florida; Mykonos, Greece; Split, Croatia).

Weather and news tabs give you an idea of the current climate (could be too hot on that Egyptian beach) and happenings, though you might come up with nothing for more obscure destinations. I also love that many of the news feeds are through Twitter accounts like @visitbritain, giving up-to-the-minute quickie items.

What will be cool about the site:

Ability to share trip ideas and plans with friends via email or Facebook is great for planning a trip with multiple people or getting feedback on a destination. Currently, Facebook Connect will tell you who you know in a given place, but I’d probably remember if I had a friend in Lutsk, Ukraine.

Festivals and special events come up via Eventful, but on the beta site event dates will pop up well after your search range so don’t plan around that blues festival just yet. There are also plans to add destination reviews, currency converters, and travel tips.

After all the searching, sorting, and sharing, you can actually book through the site, though only if you have a US credit card. The booking interface is also easy to use and gives options for frequent flier numbers, seat and meal preferences, and room types.

All in all, Wanderfly is a nifty new tool for dreaming and planning your next trip. If they could find a way to integrate time-sensitive deals, local blogs, and multiple-destination trips, this could be the only travel site you need.

I never saw myself as a cruise ship sort of traveler until MSC Musica made me a changed woman.

I’m the person who lived for two years in N’Jowara, The Gambia in a room at the back of an empty shop house without running water, window panes or electricity. Until my MSC Musica cruise, my extended boat travel was five days on the Niger River in Mali, first perched on feed sacks in a ramshackle wooden cargo boat before switching to a small boat that was poled by a man and a boy. By the time I set foot on dry land in Timbuktu, I thought of changing my name to Huck Finn.

Back in February, I wrote a post on cruise ship deals. By the end of the post, I thought “If this is such a deal, why aren’t I going?” Since one of my mom’s lifelong dreams has been to go to Greece, I put the two ideas together and searched out a cruise. The Musica, one of the ships in the MSC cruise lines fleet, seemed perfect. After one day into the cruise, I knew I picked right .

Unfortunately, my mom had had to pull out of the cruise 10 days before the ship was to depart. Fortunately, my teenage daughter was able to switch in for my mom for a $100 charge to change the ticket.

Why MSC Cruise Lines? When picking a cruise ship, know yourself and what kind of vacation you’re after. MSC is geared towards multi-generational travel. If you’re a single person looking for love, this isn’t it. If kids make you shudder, look elsewhere.

I picked this company because kids 17 and under travel for free if traveling with an adult. One kid per adult. This gave me the idea of taking my seven year old son with us. Originally, my teenage daughter hadn’t wanted to go.

Also, MSC was offering half-price deals. We were able to get a ocean view superior room with a balcony for about $1,600 per person for the 7-day cruise. If I had planned to go without my mom, I would have gone for the inside room for $999 a person.

Other pluses were the ship’s activities–most importantly, Kids Club. The ship also has an exercise room, two swimming pools, a hot tub, various food options and activities geared for people of all ages. There is a stage show each night and the shore excursions promised a wide variety of options from adventure to cultural to historical.

Because MSC is an Italian cruise line, the feel is European. This was a way to travel to Greece with an Italian twist. That also had a big role in my decision to go with this company.

With that said, if you get irritated by hearing announcements in five different languages you might get irritated. Our shore excursions were in English and sometimes in another language. When the guide was speaking in the other language, I was able to let what he or she said in English resonate. I liked this.

Food and Drinks: There were two dining options covered by the cost of the cruise. Two restaurants offered sit down meals where you ordered off the menu and one restaurant was strictly buffet. Ah, the buffet. Located on the top floor of the ship with expansive plate glass windows, the buffet called to us for breakfast and lunch. We also took fruit, yogurt, salami, cheese and bread with us from the buffet so would have a snack on our shore excursions.

During breakfast coffee and juice were included.

For dinner, we were assigned to a table at one of the dining rooms. Because there were only three of us, we were assigned to a table with two American women who were living in Vienna for the fall. Meeting up with them each evening was terrific. They seemed to enjoy us as well.

Dinner was a five-course meal of various options, My son ordered off the adult menu after deciding that the kid’s menu was too normal . At 7, he’s an adventurous eater. The food had a European bent and, in my opinion, was splendid. As a seafood fan, I had my fill. I did order one glass of wine with each meal. The $5 price was fair.

At 4 p.m. each day there was a high tea sort of offering with desserts, coffee and tea. This was also included in the set price, as was the midnight buffet. I only went to that once. On the 2nd to last night, there were ice sculptures and fruit and vegetables that had been carved into animals and flowers.

Along with the included food options, there were other specialty restaurants, but since those cost money, forget that.

I ordered one glass of wine from one of the ship’s bars on a night that I went dancing.

Every day there was a specialty mixed drink, specialty coffee with alcohol and an ice-cream treat concoction, but those cost money too. No thanks.

Before we boarded the ship in Venice, I purchased a water package and a soda package. The water package provided us with two large bottles of water each day and the soda package gave my son and daughter a soda with their dinner. We used one bottle of water at dinner and took one bottle of water with us on our shore excursion. Buying the packages made beverages less expensive. There was a wine package, but since there was only me I figured my kids didn’t need a drunk mom to take care of.

We filled other water bottles with water at breakfast and bought other water on shore.

What did we do on the ship?

I took in the free yoga lessons, stretching classes, dance classes and arts and crafts activities that were offered at various times during the day on the ship’s deck. I also worked out three times in the workout room.

Each night we went to the show that was a mix of dance, singing, acrobatic and magic acts.

My son was thrilled with Kids Club. The hours were extensive. If I had wanted to, I could have left him there when my daughter and I went on shore excursions. Taking him on shore excursions, however, was one of my trip highlights, so he came with us. He did go to the shows at night with the Kids Club gang and stayed at Kids Club doing organized activities each night until 11:00.

One bonus of Kids Club was its international flavor. My son was one of the few kids who spoke English and was the only American. This was something he enjoyed, but he is the type who will talk with anybody. Bruno and Andrea, the two adults in change of his age group were absolutely superb and offered a wide range of activities to help kids feel special and a part of the group.

My daughter was not interested in the teen activities, but was not bored. She read, hung out with me or her brother, and spent time by the pool.

Other teens I met loved the teen activities that tended to be teen driven. Games, contests, dancing–that sort of thing, were offered daily.

I did not get a massage, a facial or pay for other classes that were offered. The prices seemed fair, but I splurged on shore excursions for the three of us.

At each stop we went on an organized shore excursion. In general, shore excursions made our travel experience more meaningful. They weren’t cheap but were well worth the money we paid for them. The only excursion I thought we could have done without was the one in Athens.

From Piraeus, the port town that’s connected to Athens, taxi drivers park right outside the terminal so its possible to hire one to take you everywhere that the excursion wemt and more. Our tour was fine, but there are places I would have liked to see.

Also, the Acropolis was so crowded that we kept losing our tour guide. On the other hand, the tour guide pointed out highlights near our ship like a traditional market and a couple of churches. After our tour was over, I walked around for two hours by myself. If I hadn’t been on the tour, I would have missed them.

Here’s an Acropolis tip. Have your kids wear something red so you can pick them out from a crowd.

On the Katakolon excursion, go to Olympia and include the museum. It’s not much more money and makes the tour more meaningful.

On Santorini, we went to the black sand beach and hung out. Renting an umbrella with chairs cost $5 for the day. We took the cable car down from the town to the boat shuttles that took us back to the ship. Don’t walk along the path. Even though walking is free, the donkeys make a mess of the trail. I heard that from several people. Be warned, particularly if you like your shoes.

The Mykonos stop did not involve a tour. We ate dinner and shopped. Man, I loved this place. Look for items made from olive wood. We also started buying soap for everyone we could think of. By the end of our trip, you’d think our friends and family had a hygiene problem. I loved the soap. Soap packs easily.

At Corfu, our tour took us through the old city and then to the bay of Paleokastritza and up to a monastery. We hopped out at the beach where we took the paddle boat ride before rejoining our tour bus. From this bay you can see the small island that is supposed to be Odysseus’ ship that Poseidon turned into a rock. My daughter saw it first and was thrilled.

Dubrovnik is a gorgeous, gorgeous city that has taken care of its historical architecture. After we took the tour that included the maritime museum and the aquarium, we returned to the 2nd oldest synagogue in Europe, the oldest pharmacy in Europe and went to a gallery that pays tribute to the world’s conflicts through photographs in order to promote peace. Before we left, we had time to walk around the top of the old city walls.

Why excursions are worth the money:

The tour guides provided background history and information that we would not have found out otherwise. As we drove in the tour bus, there was a running commentary of what we were passing.

We were guaranteed we would not get lost and miss the ship. Organized tours watch your back. This lowered my stress level to zero.

Tours were a chance for us to meet and interact with other people. This made the cruise more engaging and friendly.

Because we picked tours that most interested us, we were able to gear the trip towards what we wanted to experience without wasting time at each port as we attempted to find our way.

The variety in the tour offerings made each of our days different than the rest. By the time we arrived back in Venice, I felt we had a rich overview of Greece and knew of places where I would like to return–Mykonos is number 1. Our Bari and Dubrovnik stops were splendid as well. We didn’t stay in Bari, but headed out though the rural landscape to the Crystal Caves.

Because we were on a tour, my children and I were on equal footing. I didn’t have to be in charge to get us anywhere, therefore I could just enjoy myself. Whining by any of us was a minimum.

Tips for picking shore excursions:

Let your kids pick the tours. While I was buying the water and soda packages, I let my kids go through the various tours to pick out what they wanted. I did ask them to pick a variety and not the most expensive ones. Their choices were perfect. My suggestion when picking excursions is to plan a mix where it’s not all beach and not all history. Throw some activity into the mix. On Corfu, we rented paddle boats for an hour.

Do not skimp on excursions. Each time we went to shore, I thought, we’re not going on this trip again, and I’m not missing the money I spent.

Instead, I have memories that reminds me every day at how wonderful my kids are. Sappy sounding, maybe. But, I’m telling you; this trip was worth every penny.

Bribe if you have to: I got my son to agree to walking around the top of the wall of the old city in Dubrovnik by promising to buy him something. I bought him a ceramic fish that looked like one of the fish in the aquarium we visited there. For $6, I got a bargain.

Tips in general for enjoying the cruise: Be open to experiences and people. The more easily you talk with people, the more fun you will have. Eventually, I found out that I knew or at least recognized a lot of people because I was going to classes and taking in activities.

Besides shore excursions and the glasses of wine and the beverage packages, the only other thing I bought was the professional picture taken of us on the way to dinner one night. There’s a really hokey sunset backdrop, but the three of us looked better than usual. I bought the picture for my mom. If it wasn’t for her, we wouldn’t have been on this trip.

Take time out for Venice: When booking our flights, I arranged them so we would have two nights in Venice at each end of the cruise. I wanted to give us enough time for a missed flight connection if we had bad luck, get over some jet lag and take advantage of Venice. This also allowed for travel on our own to satisfy the need for unplanned adventure at our own pace.

We stayed the first two nights at the Antico Doge, the most elegant place I’ve stayed in my life–it used to be a palace. For the two nights after our cruise we stayed at the Hotel Abbazia, a former abbey which is an excellent location near the train station, the water taxis and the bus station. Both places served a wonderful breakfast.

If you do have time in Venice, go to the Jewish Ghetto. This is the first ghetto in the world and is being revitalized by the Jewish community who live around Venice. Originally, this is where the city’s foundries were located.

Look for the tribute to the people who died in the Holocaust on one of the plaza walls. You’ll notice it because of the barbed wire. There is also a kosher restaurant that is superb. The owners just opened a guest house next door. The restaurant is located on the plaza.

With Mykonos on my mind, after reading about the mezes at Kiki’s restaurant being among the best beach food there, Strudel Monkey’s lush, gorgeous shot of Paraportiani Church on the island seemed fitting. The quality of the tones of this photo capture the essence of what I hope to experience when I go here–a certain quiet calm and a sense of timelessness. Interestingly, I’ll be there about the same time of year that Strudel Monkey was three years ago.

If you have photos to share, please load them at Gadling’s Flickr photo pool and one might be chosen as a Photo of the Day. This one is only one of Studel Monkey’s that has been granted the honor.

If you like getting naked – but don’t want to wait for an occasion – get your (bare) ass to one of the top five nude beaches in the world. From Miami to Vancouver to Mykonos to St Maarten, you’ll find a place to roam free. Thanks to TripAdvisor for pulling this together.

Haulover Beach Park – Miami Beach, FloridaMore than a million people hit Haulover every year to live the relaxed life of a nudist. If you go, you’ll stand out by trying to look like you’re not.

Wreck Beach – Vancouver, British Columbia, CanadaAt this clothing-optional beach, you’ll be able to gaze upon eagles and herons … or a whole lot of body parts you don’t normally see in public. According to one of TripAdvisor’s readers, “Wreck Beach is a magical place where I can strip off my layers of clothes and judgments, troubles and insecurities, and become one with the earth.”

Paradise Beach – Mykonos, GreeceThey’re more open-mined in Europe, right? You bet! Check out Paradise Beach in Mykonos, where you can go “swimming in the blue waters and lying on the white sand in a place where humans celebrate the good parts of life.”

Orient Beach – St. Maarten, CaribbeanHead down to the Caribbean to shed your second, unnatural skin. At Orient Beach, you can feel the sand in every orifice. According to one TripAdvisor traveler, “Orient Beach was one of the most beautiful beaches I’ve ever visited. A ‘sun worshipers’ paradise.”

Black’s Beach – San Diego, CaliforniaWatch for the cliffs, which are absolutely beautiful. Then, surf naked or simply sun the spots normally not exposed to rays.